


The One With the Special Outfits

by HolyFuckingHell



Series: Cas's List [3]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, Bottom Dean Winchester, Fluff, Fluff and Smut, Fucking, High Heels, Kink, M/M, Panties, Panty Kink, Sex, Smut, Top Castiel (Supernatural), Top Castiel/Bottom Dean Winchester
Language: English
Status: Completed
Published: 2020-09-10
Updated: 2020-09-10
Packaged: 2021-03-06 20:01:55
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,050
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26394589
Author URL: https://archiveofourown.org/users/HolyFuckingHell/pseuds/HolyFuckingHell
Summary: A few days ago, Dean pointed out something on Cas's list that needs a bit of preparation. Now, as soon as they see each other they can't keep their hands off. (Not that they need to) It's not their fault, it's what they're wearing!
Relationships: Castiel & Dean Winchester, Castiel/Dean Winchester
Series: Cas's List [3]
Series URL: https://archiveofourown.org/series/1887445
Comments: 14
Kudos: 150





	The One With the Special Outfits

**Author's Note:**

> What is this, part three?

“Dean, come in! I want to see,” Cas says, sitting on Dean’s bed, waiting.

“You first!” Dean shouts back from the other side of the door. 

“Dean,” Cas thinks, “That doesn’t make sense. I am the one in your room, you need to come in, how could I do it first?”

“I want to see you first…” Dean mumbles, but Cas hears.

“When you walk in, we are going to see each other at the same time.”

“Are you wearing it?” Dean shouts.

“Yes.”

“And the-”

“Yes, Dean. Just walk in before I meet you in the hallway.” Ahh, hallway sex. Sex you have when you can’t wait to go those extra few last steps to make it to the bed. Or even to the room for that matter. Dean considers for a moment.

“Close your eyes…” Dean says nervously. 

“Why?” Cas asks, closing his eyes. 

“Because I want to see you first! I’ll tell you when to open them…” Dean paces back and forth a little bit outside the door nervously, He has been since he got ready. “Are they closed?”

“Yes,” Cas says honestly. 

“Okay,” Dean opens the door and sees Cas sitting on his bed. “Holy fucking hell,” Dean says slowly as he admires Cas. Cas is wearing three things. Only three things. One, he’s wearing his tie. Two, he’s wearing a pair of light blue, soft cotton panties with black lace on the top half and around for the trim. And three, black high heels, plain black. “Cas you look-” Dean doesn’t know what to say. Cas is sitting on his bed like he’s trying to present himself. His legs are apart, his arms are back, and he looks very relaxed.

Dean gets onto Cas’s lap, straddling him, and starts kissing him. Their bare chests rub together and Cas lifts one arm up and slides it all over Dean’s back because, at the very least, Cas loves to touch Dean. He leaves the other arm back to support himself up, and now Dean as well. “Do I-” Cas says quickly in between kisses, “Get to see… you?”

Dean pulls away, pausing on Cas’s lap for a few seconds. “Fine.” 

Cas hasn’t opened his eyes yet to keep his promise with Dean. “Aren’t you going to stand up? So I can see you?” Cas may not have been nervous about this, but Dean sure has been. Has been for the past 48ish hours. 

About two days ago, Dean and Cas were sitting in his room. Dean looks over at Cas, “Cas, can I see that kink catalog?”

Cas reaches into the pocket of his trench coat, “Yes, why?” He passes a folded up piece of paper to Dean and Dean opens it. “Do you have another idea for it?”

“No… I don’t think so. I just wanna see it again.” Dean starts reading through the list trying to remember what Cas said they all were. Notices that Cas had put a neat line through ‘sex outside’ to where you knew it had been done, but you could still read what it said. 

“Do you want to try something on it?”

“I want to try  _ everything _ on it,” Dean says, like it obvious, “What is this one again?” 

Cas looks over and replies, “Dean, I already told you that I am not going to tell you.”

“I know,” Dean sighs, “Just thought I’d ask.” Dean points to another word and holds it out for Cas to see, “We should do this one!”  
“Altocalciphilia, alright.” Cas agrees, “We can’t do it right now though,” Cas continues, “I am not prepared with the proper things for it yet.”

“Me either,” Dean agrees.

“I thought you had a collection of women’s underwear…”

“Panties,” Dean corrects, “And yeah I do, but I don’t have high heels, isn’t that what this word means anyway?” Cas nods, “So we both need to get some then… You can-” Dean swallows and averts his gaze, “You can wear… one of my… pair… if you want.”

Cas smiles, “Thank you, but I want my own,” Cas says sounding cold. 

“Ohh,” Dean says with a sad tone.

“To surprise you,” Cas adds.

“Ohh!” Dean says a bit more cheerfully. “So we gotta go separately then.”

“Okay!” Cas gets on board, “Let’s say that in… two days, if we aren’t busy,” Cas is referring to a hunt that could pop up at any minute or anything along those lines, “Then we try it.”

“Okay,” Dean smiles and nods, looking back to the list, “Two days!”

“Alright,” Cas smiles.

Dean looks curiously at the list, “Cas… what was this?” He points to what looks like another small word written at the bottom that is scribbled out. It’s next to the other scribble.

“What is what?” 

“This word, at the bottom…” Dean trails off and tries to read through the scribble, “U… U… No, W…” Cas snatches the paper away from Dean again and folds it quickly. “Cas!” Dean shouts from the initial shock. “Did you write the same thing again?”

“Yes, but I scratched it out again so you do not need to worry about it. Or look at it. Or try to read it. Or ask about it.”

“Cas, just tell me what it is,” Dean says sympathetically, “You obviously want to try it, you wrote it down twice.”

“I don’t want to try it. I scribbled it out twice.”

Dean rolls his eyes, “Okay,” He says remembering how Cas reacted the first time, so seriously. Dean figures he better change the subject, “Two days though…” 

“I’ll be ready,” Cas says surly. 

“Me, too. But that doesn’t mean we can’t do anything… right now…”

So one very fun night and almost two days later, Cas talks to Sam. Sam, learning way too much and still trying to learn as least as possible, quickly agrees with Cas to take Jack and go  _ anywhere _ to give Cas and Dean the bunker to themselves for a couple of hours of pure privacy. 

Dean gets up off of Cas and stands up in front of him. He nervously holds onto his arm with one hand, “Okay… I guess you can open your eyes,” Dean says shyly. 

Cas opens his eyes very quickly, excited to see Dean. Cas looks Dean up and down silently. He looks panicked down at his own lap then back up at Dean with wide eyes. 

“What?” Dean says insecurely.

“I um-” Cas looks down and back up again, “I have an erection,” Cas says like it’s a problem. 

Dean starts to smirk at Cas’s forward words that he finds hot for a reason unbeknownst to him, “Okay… Do I not usually turn you on or something?”

“No! It’s not that!” Cas says quickly. “Wow,” Cas looks at Dean again, “It’s just that I never get erect for a reason like this…”

“Cas, I was hard the literal second I walked in. I saw you and boom,” Dean points up as a gesture, “Got sprung.”

“I noticed. It looks very arousing through the panties you chose… Well, it’s not this easy for me… usually. It takes more than this... It takes friction or something… this… this-” Cas stutters, “This is embarrassing!” 

“Now you know how I feel, Cas,” Dean chuckles, walking over to his drawer to get lube. “It’s not a bad thing, it’s actually kinda flattering.”

Cas looks at Dean and marvels at him. He’s wearing lacy, purple panties that come up pretty high on his waist and are tight on his ass and can hardly contain his half-hard cock and it’s driving Cas crazy. All the way down to the tiny white bow in the front. And then Dean is wearing white high heels. Higher than Cas’s heels. And they make his legs look so strong and no wonder Cas is already hard. “Dean you look amazing…” Cas says. 

Dean walks back to where Cas is and mumbles, “Don’t you fucking know it,” and squats down between Cas’s legs. Dean has gained a lot of confidence based on Cas' reaction. He realizes he should have had it all along because he knows he looks good. His nerves stemmed from excitement. 

“I have an honest question, how do you walk and  _ squat _ so well in your heels, Dean?” 

“I know right?” Dean says, “I was horrified at how good I was but then I figured it just must not be that hard.”

“It’s difficult Dean, very difficult,” Cas informs.

“Well, maybe I was made for them, I don’t know,” Dean lets out a hot breath against Cas’s clothed dick and Cas sighs deeply, “This is going to be more fun than I thought,” Dean does it again, “We should have been doing this the whole time,” Dean starts mouthing hotly at Cas’s cock through his panties, flicking his tongue out occasionally to get them wet.

Cas hums, “I want to be inside of you, Dean. Again and again, gently until you can’t handle it anymore,” Dean moans loudly and deliberately, open-mouthed around Cas’s cock, “And you come and make a mess,” Dean pulls the top of Cas’s panties how exposing just barely the tip of his hard dick and Dean licks at it, “Hmm…” Cas hums, “And then I want to keep going until I come or you beg me to stop…”

“I want you to come, but I’ll still beg if you want… Beg you to keep going...” Dean stands up and straddles Cas again and they resume their previous kissing, “Cas, you look so hot,” Dean says quickly, briefly pausing.

Cas wraps his arms around him and rolls him over so he is on top of Dean, “I have to get you open,” Cas says to Dean, but mostly to himself. “Move up the bed,” Cas instructs Dean. Dean, as quickly as he can, scoots up on the bed so his feet are no longer dangling off. “I am very attracted to you right now,” Cas says kneeling at his feet. “Put your hands above your head,” Cas requests. “Yes…” Cas hums, “Now cross your wrists over each other…” Dean does. “Hmm,” Cas grumbles lowly with a smile, “I should have tied you down.”

“Not too late…” Dean suggests. 

“There’s no time, you are just going to have to be good and keep your hands there,” Cas says quickly, picking up the lube. 

“You can move these out of the way, they’re stretchy,” Dean tells Cas, talking about his panties. 

“Would you rather me move them or take them off of you?” Cas asks quickly.

Dean pants, “Up to you,” Dean bends his knees up and spreads his legs a little more. Cas puts lube on his fingertips and with his other hand, he slides the panties out of the way so he can smear the lube over Dean’s hole. “Hmh!” Dean whines at Cas’s soft touch, “Cold,” Dean mumbles. It’s a nice feeling of the cold lube on him followed by Cas’s extremely warm fingers that push in after. Dean moans and starts wiggling smally on the bed. 

Cas smiles, “You chose your attire well, Dean,” Cas commends, “I couldn’t have imagined anything better… You look fantastic…” Cas hums, “Wow.”

Dean tries to grind his hips down on Cas’s fingers which lets Cas know he wants more so he adds a third finger. “Cas,” Dean moans. 

Cas drags his fingers of his free hand over Dean’s lower stomach, back and forth. “Does it feel good when you do that?”

“When I do what?” Dean breathes out, “Fuck onto your fingers?” Cas licks his lips and nods. Dean smirks, “Yeah it does…”

“Do it again,” Cas suggests. 

“It’s kinda hard,” Dean grunts out, followed by a moan when Cas pushes his fingers in farther than before.

“Try.” Dean arches his back and grinds down on Cas’s fingers again and another moan comes out. “Good,” Cas applauds, “Again.” Dean shuts his eyes and does it again with a grunt. Cas smiles, “Again.” Dean grinds down again. “One more time, Dean,” Dean grinds down and whines Cas’s name. “Mmm,” Cas hums. Cas glides his hand up Dean’s chest and traces Dean’s bottom lip with his thumb until Dean opens his mouth and starts licking at it. Cas, who is now pleasantly surprised, takes his thumb out of his mouth and starts rubbing it against one of Dean’s nipples. 

Dean’s eyes flutter open looking at Cas’s body up and down. Dean figured he would like to see Cas in panties but he didn’t expect to like seeing the heels as much as he does. It’s nice. “Cas,” Dean moans, “You look-” Dean shrugs and chuckles, “Just so hot,” He laughs. Cas smirks and moves his hand down to feel Dean’s bulge through his panties. He rubs softly along it, so smooth and firm. “Cas,” Dean pushes out, “I think I’m ready for you to be inside me now,” Dean admits. 

Cas pulls his fingers out of Dean, “I know.” Cas lifts Dean’s legs up. It’s weird, Dean being able to see heels in the air and they’re  _ his _ . It’s not bad, it's just different. And new. And the weird part is he likes it. He glances down and can sort of see Cas’s heels too. Okay, so he really likes it. 

Cas starts pulling his underwear down. “No!” Dean shouts hastily, “Don’t take them off!” Cas stops what he’s doing and looks at Dean. “Pull your dick out, but leave them on!” Cas adjusts his panties and pulls his dick out of one of the legs holes instead of the top which makes Dean chuckle, “Interesting choice,” He pants, “Ready when you are.”

Cas slides into Dean very slowly and hums while Dean squeaks. “Why is it interesting?”

“I thought-” Dean can’t really talk, “You were gonna do it differently,” He moans, “It’s good!”

Cas starts moving gently in and out, “You are so attractive,” Cas says, eyes still constantly wandering all over Dean’s body. “Hah,” Cas moans. 

Dean’s eyes widen, “Please make more noises,” Dean asks. Dean really likes to hear all kinds of noises that Cas makes and Cas obviously knows that. He doesn’t ask Cas to do it all the time so Cas figures since no one is here, he might as well not hold back. 

Cas speeds up his thrusting, “Ughh, Dean…” Cas groans. Dean squeaks. Cas then decides to bend down and try to kiss Dean. Dean is pleasantly surprised to see that he is still flexible enough to do this with Cas. If asked before this moment, he would have said that _no,_ _his knees could not bend back to his head_. Even though he can do it, it isn’t super comfortable. But, Cas wants to kiss, so they are gonna kiss, it is what it is. 

Cas’s thrusts have become shorter now that they are like this, Dean doesn’t mind though, he really tries to focus on Cas’s lips… and tongue. And now he realizes he needs to focus not dying from lack of air. Dean turns his head slightly and pants but Cas’s get right back to it. “Ohh, Dean,” Cas moans, barely leaving any space between their lips. “Always so tight, mmm…” 

“Always so big,” Dean grunts.

Cas licks along Dean’s bottom lip and Dean smashes their mouths back together into another kiss, “Mpf, mmm,” Cas whines. 

Dean reaches a hand to the back of Cas’s head and into his hair when Cas suddenly pulls away, grabbing Dean’s wrist and slamming it back above his head, “No,” Cas says sternly, “Be good, Dean. Try to remember.” Cas leans back to how he was before which is relieving for Dean’s legs but not so much his lips. Cas thrusts harder and less gentle.

“Gah!” Dean shouts. “Yeah, keep-” Dean doesn’t finish his sentence but Cas, of course, knows he wants him to continue on like this, Dean likes it rough. “Oh  _ fuck _ !” Dean screams.

“Ngh,” Cas grunts, “So beautiful.”

Dean wiggles slightly, “Hahhh…” His back arches off the bed, “Cas, I’m gonna…  _ fuck _ !”

“You’re going to ejaculate in those nice panties, Dean?” Cas coaxes, “Drench them, mess them up, get them so filthy…” 

Dean comes with a loud moan, louder than usual because he doesn’t have to be quiet and he knows that. Cas fucks into him repeatedly throughout his orgasm then stops once he’s done. “You can- Cas, seriously, it’s- okay,” Dean pants. 

Cas thrusts into Dean, “Are you sure?” Cas asks, concerned. 

Dean is already feeling very sensitive and he moans loudly, “Yeah, just keep-” Dean squeezes his eyes shut, “Going.”

“Tell me to stop at any time,” Cas reminds him and keeps thrusting into Dean. 

“Fuck!” Dean wails. “Ahahhh…” 

“I’m going to stop.”

“Don’t stop!” Dean shouts, “Look, I didn’t think I would-” Dean moans, “actually… beg... But please, Cas!” Dean pants, “Keep going. I’m okay! Just, keep…” Dean grunts and his eyes start to water a little bit. 

“Dean, your shaking.”

“Damn it, Cas!’ Dean shouts, trapping Cas with his legs and flipping them over. “I told you-” Dean huffs, resituating them. “I’m fine!” Dean lifts his hips up shakily and slams them back down onto Cas, “Just come when-” 

“Hmm!” Cas moans.

“When you feel like it!” Dean lets out a whine that Cas would be worried about if Dean had not just rolled his hips. Dean almost non-stop makes tiny wincing and whining noises. Cas reaches his hand up to Dean’s waists and his thumbs feel along the lace of Dean’s panties, back and forth. 

“Dean, I’m close,” Cas says to Dean. 

Dean is relieved because he doesn’t know how long he can keep this up. He’s so sensitive right now he feels like he might explode and he’s shaking so bad that he looks like he replaced sleep with coffee. Dean’s fists are balled pushing against Cas’s chest to hold him up. “Make more noise,” Dean says quickly through an exhale. 

He instantly starts moaning again. Every time Dean drives down Cas lets out a little moan. “I’m coming,” Cas says half calmly.

The second Cas is done, Dean comes off of him and lays down next to him. Dean, who is still shaking, wraps an arm around him and pulls Cas’s body into his. “Fuck!” Dean groans and pants, “holy fuck!”

Cas wants to kiss Dean again but knows he has to breathe. Cas fixes his awkward panties to fit right again, putting his dick back into them. “You can take your shoes off,” Cas says to Dean. Dean exhales loudly, “Or I could take them off for you…” 

“But I look-” Dean pants, “Cock-lifting good in them,” Dean smiles.

“You do,” Cas agrees. “It’s strange.”

“Why?” Dean asks judgmentally. Of course, he looks good in them.

“I expected you to like them more than me, but I suppose I was wrong,” Cas explains. 

“I’d say,” Dean breaks, “It was pretty even.”

“You look very attractive in what you’re wearing.”

“You, too,” Dean says. “When I saw that you still had on,” Dean swallows, “Your tie? I coulda come on the spot.” Dean seems to be breathing a bit more normally. 

“Now you’re exaggerating, but I appreciate it,” Cas rolls onto his side and starts kissing Dean again. 

They kiss for a while, actually. By the time they stop, Cas is lying completely on top of Dean and their legs are tangled together, heels and all. 

“Your panties are getting mine dirty,” Cas says bluntly.

“Then clean them,” Dean challenges. Cas rolls his eyes but does. “I’m so glad you came when you did… I didn’t think I could handle any more.”

Cas lifts his head and squints at Dean, “ _ You said you were fine!” _

“Yeah! Of course I said that! You were gonna stop!”

“ _ Dean! _ ” 

“What? Look at me, I am fine!” Dean defends. “You know how sensitive I get. It was almost unbearable…”

“Dean!”

“ _ I said  _ almost _!”  _ Dean attests. “What could have happened, why are you so worried?”

“Were you in pain?” Cas asks, honestly worried. “Do not lie! I know if you’re lying.”

“No, of course not,” Dean says, “It’s just this feeling that… has no outlet, you know what I’m talking about! It’s just a lot.”

Cas actually does  _ not _ know what Dean is talking about, but he knows whatever he is saying is the truth. Cas lays his head back down and lets it go fairly quickly when he looks over at Dean’s nipple. He smirks and then licks it very sloppy before he blows cold air onto it. He smiles when it perks up. “Do you remember talking to me about your perky nipples a few months ago?” Cas asks Dean. 

“What?” Dean chuckles, “No…”

“That makes sense, you were highly inebriated. And as a result, you were goofy. You also, unfortunately, told Jack as well…”

“That never-” Dean tries to remember, “Huh. No actually, that could have happened.” Dean cringes, “Oh gees, did that really happen?”

“Why would I make that up?” 

“Okay, so if it did, why’d I say it?” 

“It was cold in the library when you walked in and you bumped into Jack and said ‘Cas, look, my nipples are hard!’ and then you laughed.” Cas smiles, “Then you looked at Jack and realized he was not me and said, ‘You’re not Cas, sorry.’”

“Where were you?” Dean asks. 

“I was sitting across the room! Then you noticed that I was and continued on like Jack was not there. ‘See Cas? I have perky nipples…’ and then I chuckled and you pulled on your tshirt and puffed your chest out so I could see and you kept going-”

“Okay, that’s actually embarrassing, I don’t even remember- oh fuck,” Dean stops. “And then I said ‘I have the perkiest nipples and here’s the proof!’”

“‘Ask anybody!’ you said,” Cas starts to chuckle. “But then Jack started to think it was funny until you started-”

“Oh, fuck I said what I liked,” Dean says mortified.

“You said, ‘Cas, you know!’ and you walked over to me and you sat in my lap facing me and then you happily said way too loud, ‘I like when you touch them, and rub them, and pinch them, and lick them, and suck-’ and then you hiccuped and I suppose you lost your thought because you just stopped.”

“That is horrible,” Dean states. 

“Then you hugged me and said into my ear what I think you meant to whisper,  _ but it was not _ a whisper, ‘I’m gonna godda bed,’ and you got up and-”

“And went to bed, yeah…” Dean remembers. “Why do you mention it? You know, I probably would have forgotten if you hadn’t reminded me.”

“Because I love the way your body responds to different actions…” Cas smiles. “Oh, Dean! I just had an idea!” Cas says quickly and sits up. He sits at the end of the bed and pulls off his shoes and drops them on the ground. 

“Idea for what?” 

Cas scrambles to get his coat. He has all his clothes neatly folded on Dean’s desk so it’s easy to find. He unfurls it enough to reach into the pocket and grab the list. He quickly finds a black pen and begins writing. “We are going to have sex when we are both inebriated. Wildy.”

“Sex wildly?” Dean says excitedly.

Cas laughs, “Inhibrated wildly,” he chuckles again. 

“Ohh.”

“If you want,” Cas looks up at Dean.

“Sure, yeah. Absolutely. One thing though, how are we gonna get  _ you _ drunk?”

Cas starts writing again, “With a lot of effort.” Cas finishes up and slides the paper back into his pocket and walks back over to Dean. “Do you want to say goodnight to Sam and Jack or do you want to just stay in here?” Dean pulls Dean’s shoes off for him. 

“They’re back?” 

“I heard the door open and slam shut so I am going to say yes.”

“Let’s just stay, we’re both in our underwear and I’m feeling a little touch starved right now,” Dean smirks.

“How could I let that happen?” Cas says dramatically and lays on top of Dean again.

Dean wraps his arms around Cas, “There we go…” Dean breathes out.

“You have the perkiest nipples and here’s the proof!” Cas mocks. 

“Okay!” Dean rolls his eyes with a smile. 

**Author's Note:**

> Sorry that these are kinda long, I aim for like a max word count of 3500 most the time, but obviously I'm failing. Let me know if it's bugging you and y'all want them shorter, if not then were all good!
> 
> Please please please comment! I love to hear what y'all are thinking. I check constantly for DAYS. It can be anything! Let e know if y'all have ideas, I would love to hear them!


End file.
